


Obligatory Crossdressing Episode

by Redawilo



Category: Pocket Monsters | Pokemon - All Media Types, Pocket Monsters: Sword & Shield | Pokemon Sword & Shield Versions
Genre: Crack Fic, Crossdressing, M/M, Piers might be lowkey morosexual, Raihan and Leon are too dumb to live, Swearing
Language: English
Status: Completed
Published: 2020-11-23
Updated: 2020-11-23
Packaged: 2021-03-10 06:34:20
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,554
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27689009
Author URL: https://archiveofourown.org/users/Redawilo/pseuds/Redawilo
Summary: Raihan fucked up and now his two boyfriends have to cross dress for a party.---You know how anime in around the 90s would have that one episode where all the guys have to cross dress and often times were really bad at it? That was basically my inspiration for this.
Relationships: Dande | Leon/Kibana | Raihan, Dande | Leon/Kibana | Raihan/Nezu | Piers, Dande | Leon/Nezu | Piers, Kibana | Raihan/Nezu | Piers
Comments: 6
Kudos: 38





	Obligatory Crossdressing Episode

**Author's Note:**

> So basically I saw a piece of fanart that looked like Leon was about to do the anime rich girl laugh and somehow that led to this. X'D I hope you all enjoy.

It all started one fateful afternoon just after lunch…

**dragonborn:** I FUCKED UP!  
 **dragonborn:** HELP!  
 **zigzagblep:** what else is new?  
 **hatrizard:** Raihan, please explain.  
 **dragonborn:** I GOT INVITED TO A PARTY IN HAMMERLOCKE AND EVERYONE WAS SAYING I HAD TO BRING A DATE AND I FELT LIKE BRAGGING SO I SAID I WAS GOING TO BRING THE PRETTIEST GIRLS IN GALAR!  
 **hatrizard:** Raihan…you’re gay…  
 **dragonborn:** I KNOW!  
 **dragonborn:** BUT THEY DON’T!  
 **dragonborn:** _I FUCKED UP!_  
 **zigzagblep:** couldnt you just come clean and tell em that youve got 2 boyfriends?  
 **dragonborn:** IT’S TOO LATE FOR THAT!  
 **dragonborn:** THE PARTY IS IN TWO DAYS!  
 **dragonborn:** HELP!!!!!!  
 **zigzagblep:** alright calm down  
 **zigzagblep:** well help  
 **hatrizard:** Yeah! It’ll be alright. Piers and I will dress up!  
 **zigzagblep:** wut  
 **dragonborn:** THANK YOOOOUUUU!!!!  
 **dragonborn:** Come to my place and we’ll figure all of this out  
 **zigzagblep:** no really, wut???  
 **hatrizard:** No problem! I’ll be there tonight!

And that was how Leon and Piers came to arrive at Raihan’s home late one evening. Once they’d arrived Raihan showed them the invitation he’d received and the text messages he’d had with the group. He explained that the party wasn’t hosted by friends of his, but they were all affiliated with Hammerlocke’s higher society. The whole reason he had been invited was because he was the gym leader and was of course immensely popular. Several of the group had been stroking his ego and asking about what sort of person he was going to bring as a date. That was when the man had decided that saying he would bring pretty girls was a bright idea.

Piers groaned. “Rai, this invitation was sent _a month ago_. Why’re you just now telling us about this?!”

“I was panicking, okay!? I thought maybe if I waited I would come up with something!”

Leon gave him a pat on the shoulder. “It’s okay. Like I said, Piers and I will help you. Now, do you at least have something for you to wear?”

The gym leader nodded. “They said it’d be perfect if I wore my gym uniform…”

“Well, that’s a step in the right direction. Piers? Did you bring the clothes for us?”

Despite the absurdity of it all, Piers had in fact brought along with him several dresses, makeup, and accessories for him and Leon to make use of. No one asked him where he’d gotten them from, and quite frankly he was glad for that. The tales of what laid buried deep in his closet were probably too much for the world to know. Even for him.

Which meant he’d forgotten where he got most of them.

The next two hours were spent trying on the dresses. They sorted them into three piles; ones that might fit Piers, ones that might fit Leon, and ones that wouldn’t fit either of them. One by one the two men did their best to put on the ones they thought might work. Then they either discarded them because they didn’t fit or they stepped out in front of the other two to get the collective opinion on it.

Somehow or another this landed Piers in something that wouldn’t be out of place in a Gothic Lolita’s wardrobe and Leon in a deep red form-fitting dress that was cut _way_ too low on the chest and whose skirt only came to mid-thigh.

Seeing how late it was, they decided to call it a night there.

But the following morning they went right back to it. The next step on the agenda was to get Leon walking in a pair of heels. Luckily, Piers owned a pair that not only fit the former champion but also went well with the dress. As if it weren’t enough, Raihan also got pulled into learning because Piers reasoned that it was unfair for Leon to take on most of the burden. The singer was kind enough to give them a quick demonstration, verbally and visually pointing out the key factors in remaining steady on one’s elevated feet. Then it was time for the other two men to give it a go.

Unfortunately it didn’t turn out _quite_ as funny as he had hoped, seeing as it meant he had _two_ wobbly-legged men to hold steady and walk with like a couple of overgrown babies taking their first steps. It only took a collective fifty-three slips and fourteen falls for the two men to be able to walk across Raihan’s living room and back without fucking up _and_ appearing steady enough on their feet. So really it was still funny and Piers felt tried from laughing at his poor fools-for-boyfriends so much.

With the dresses and walking in heels covered, it was time to move onto the final step in their preparation: makeup. Piers assured them that he had his own covered and neither of his boyfriends questioned it. But for Leon, they had him put the dress back on and sit him down so that the singer could experiment and work his magic.

It didn’t help that the man kept squirming and trying to tug the skirt of his dress down. Getting frustrated with his moving around, Piers scolded him and told him to sit still!

“I can’t!” the man complained. “Piers, this isn’t going to work!”

“It was your idea, though!”

“I know! But I can’t walk and I can’t sit down. How do women do this?!”

“Well for one they _close their legs_ , you slob!”

“THEY HOP!?”

Raihan erupted into laughter.

“Oh my fucking Arceus why am I dating you…?”

After carefully explaining to Leon that women keep their legs closed while _sitting_ so that their skirts don’t ride up and expose anything, Piers clamped the former champion’s legs together between his own knees and resumed his work on the man’s makeup.

At last, Piers managed to pull together a look that both he and Raihan were happy with. Leon begged them to get him a mirror to show him, but Piers refused it. He said that he would just have to wait for all the pictures that Raihan was bound to take during the party.

And then came the actual day of the party. Piers made sure that Leon was all dressed and prettied up, including braiding his hair and slipping a few red and white flowers into it for decoration. He then went and took care of himself. Despite how ridiculous he felt, he could tell he’d nailed the look by the way his boyfriends’ eyes lit up when he joined them in the living room. Raihan got himself dressed and Piers made a few minor adjustments to his hair and even did a little bit with makeup just to ensure that he lived up to the expectations of those who had invited him.

They arrived at the party by flying taxi. The flyer had given the three of them a puzzled look, but hadn’t said a word. Upon arriving Raihan was greeted warmly and Leon and Piers were asked for their names. Leon and Raihan panicked, as neither had thought about names.

Luckily for them Piers had been thinking ahead. _Somebody_ had to. “This is Leona, and my name is Patricia.”

The two men promised to kiss him later for saving their asses.

The party went well, all things considered. Leon didn’t slip and fall, although there were a few times where he had clearly stepped wrong and wobbled because of it. He also remembered to keep his legs together when he sat down. Honestly his performance was overall passable except for the fact that he kept laughing like a rich girl in an anime. But nobody said anything about it, so it was fine. And for his part Piers didn’t really try to do anything. The dress was a bit bulky and cumbersome, but it wasn’t anything he couldn’t deal with. Because of his own nature he didn’t do much talking, which was fine because his boyfriends were both outgoing enough to make up for it.

The night ended with every couple or group getting their pictures taken by the host couple, just as a way for them to preserve the memories. Raihan happily had one of his “girlfriends” on each arm, and both of them were happy to have made his night less of a screw up than it could have been.

They crashed at Raihan’s place after the party that night. In the morning while Piers made them breakfast, the gym leader skimmed the news and social media on his phone…mostly social media. All of a sudden he stopped dead and stared in horror.

“Um…loves? I hate to tell you this, but…” he turned his phone around to show them all the posts he’d just seen. “Everyone at that party knew it was you two…”

Leon flushed and appeared just as terrified as Raihan did. Piers took a quick glance and shrugged.

“I could’ve told you that. Who the fuck else has hair like mine? Not to mention Leon still had his beard and all of his chest hair on display all night.”

Realization dawned on the two taller men.

And Piers just smiled as they began to freak out and ask him why he hadn’t said anything earlier.

He really did love both of the dumbasses he was dating.

**Author's Note:**

> I could probably have made this fic like four times better in quality but honestly I don't care I just had to share it with everyone. Let me know what you thought of it!!


End file.
